Coffee With Chris: Stories on Grit, Growth and Leadership

Coffee with Chris

Weekly reflections on life, leadership and finding peace in the chaos...from my pond straight to your inbox.

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Your Superpower might be simpler than you think...

There’s a pattern I’ve started to notice in my career… Superpowers are a thing. I’m usually not the smartest person in the room...like ever. I’m not the technical expert (those who know me can stop laughing any time now)... And I’m rarely the one building the product... But I do seem to have one ...

by Chris Errington — Mar 28, 2026

Why Trust Matters More Than Titles

One quiet goal I have these days. I want to be someone people trust without hesitation. Not because of a title...not because of a position... Just because of who I am. That might sound simple, but the older I get the more I realize how rare that kind of trust actually is. Most of the world is bui...

by Chris Errington — Mar 21, 2026

Maybe We've Been Asking the Wrong Question?

How on earth is that possible? And it’s not like I’ve never been asked. That question has been coming at me for decades now…usually from people who had their lives figured out far earlier than I did. “What do you want to be when you grow up?” When I was a kid, I had the same big dreams most kids ...

by Chris Errington — Mar 14, 2026

Live Like You Were Dying…Or Just Stop Pretending You’re Not

I heard “Live Like You Were Dying” again this week... Not intentionally...it just came on. And I didn’t hear adventure this time...I heard prioritization. When you strip the song down, it isn’t about skydiving or mountain climbing. It’s about focus. When the noise drops…When the timeline shortens...

by Chris Errington — Feb 28, 2026

50 Feels Different Than I Thought

I turned 50 this week. And for most of my life, I assumed that number would feel different. At 20, I thought success at 50 would be obvious. Big bank accounts...Fancy cars...Dream homes and vacations... External markers that told the world I had “made it.” Instead, what overwhelmed me wasn’t reve...

by Chris Errington — Feb 21, 2026

When failure feels louder than reality

There’s a specific kind of tired that shows up after disappointment. Not physical...narrative. It’s the exhaustion that comes from replaying moments you wish had gone differently. Conversations.Decisions.Silences. Failure doesn’t usually arrive with fireworks...it sneaks in quietly…and then your ...

by Chris Errington — Feb 14, 2026

Time Isn’t Patient

“Don’t behave as if you are destined to live forever.” Read it again. Not because it’s dramatic...but because it’s practical. Most damage isn’t done by bad intent...it’s done by delay. We postpone conversations.We defer decisions.We tolerate misalignment longer than we should. All because we assu...

by Chris Errington — Feb 07, 2026

Getting Up Matters More Than How Hard You Fell

Chris Errington | Your Sales Wingman Chris Errington...E2E Solutions Ltd...Network strategy... shipper and carrier partnerships... sales coaching... practical systems that mo... www.chriserrington.com There’s a moment most people don’t talk about. It’s not the fall. It’s the moment you r...

by Chris Errington — Jan 31, 2026

You Don’t Get Away With Things… You Just Delay the Receipt

Chris Errington | Your Sales Wingman Chris Errington...E2E Solutions Ltd...Network strategy... shipper and carrier partnerships... sales coaching... practical systems that mo... www.chriserrington.com There’s a belief floating around that karma is some mystical force... I don’t see it th...

by Chris Errington — Jan 24, 2026

Coffee with Chris...Maybe the Stoics Were Right About Time

I read a line from Marcus Aurelius that I just can't shake... “Am I afraid of death because I won’t be able to do this anymore?” It haunts me now... When I first read it, I thought about our kids...the girls chasing their dance dreams...Bubba chasing baseball glory... Most would call them long ...

Jan 10, 2026

Maybe So...Maybe Not...

There's an old story often told by Alan Watts... It's simple…almost too simple...and that is why it cuts so deep when you sit with it. A farmer lives with his son and a single horse. One day the horse runs away...the neighbors gather and say…“Such bad luck.” The farmer replies…"Maybe so…maybe not...

by Chris Errington — Jan 03, 2026

2026… The Year You Finally Build the Life You Keep Talking About

There used to be a moment at the end of every December where I felt that quiet tension in my chest... The year is almost over…the next one is knocking at your door…and you start asking the same question every person asks… “What am I going to do differently next year?” Most people answer with re...

by Chris Errington — Dec 27, 2025

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